In silico strategies for modeling stereoselective metabolism of pyrethroids

ACS Symposium Series

Volumn 1099, Issue , 2012, Pages 245-269

  Chang, Daniel T ^a   Goldsmith, Michael Rock ^a   Tornero Velez, Rogelio ^a   Tan, Yu Mei ^a   Grulke, Christopher M ^a   Chen, Ling Jen ^b   Ulrich, Elin M ^a   Lindstrom, Andrew B ^a   Pasquinelli, Melissa A ^c   Rabinowitz, James R ^a   Dary, Curtis C ^a  

^a U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^b ALION SCIENCE AND TECHNOLOGY   (United States)

^c NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FORECASTING; HYDROLYSIS; METABOLISM; MOLECULAR GRAPHICS; PESTICIDES; PHARMACODYNAMICS; RATE CONSTANTS; RISK ASSESSMENT; STEREOSELECTIVITY; SUBSTRATES;

CARBOXYLESTERASES; METABOLIC PROCESS; MISCLASSIFICATIONS; MODEL DEVELOPMENT; PYRETHROID PESTICIDE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS; STEREO-SELECTIVE; STEREOCHEMICAL PROCESS;

COMPUTATIONAL CHEMISTRY;

EID: 84905658108     PISSN: 00976156     EISSN: 19475918     Source Type: Book Series    
DOI: 10.1021/bk-2012-1099.ch016     Document Type: Conference Paper

References (64)

1. Dennison, J. E.; Bigelow, P. L.; Mumtaz, M. M.; Andersen, M. E.; Dobrev, I. D.; Yang, R. S. J. Occup. Environ. Hyg. 2005, 2 (3), 127-35.
2. Jang, J. Y.; Droz, P. O.; Kim, S. Int. Arch. Occup. Environ. Health 2001, 74 (1), 31-7.
3. Clewell, H. I.; Gentry, P. R.; Gearhart, J. M.; Allen, B. C.; Andersen, M. E. Sei. Total Environ. 2001, 274 (1-3), 37-66.
4. Cantoreggi, S.; Keller, D. A. Toxicol. Appl. Pharmacol. 1997, 143 (1), 130-9.
5. Corley, R. A.; Mendrala, A. L.; Smith, F. A.; Staats, D. A.; Gargas, M. L.; Conolly, R. B.; Andersen, M. E.; Reitz, R. H. Toxicol. Appl. Pharmacol. 1990, 103 (3), 512-27.
6. Loizou, G. D. Toxicol. Lett. 2001, 124 (1-3), 59-69.
7. Tornero-Velez, R.; Rappaport, S. M. Toxicol. Sei. 2001, 64 (2), 151-61.
8. Tan, Y. M.; Sobus, J.; Chang, D.; Tornero-Velez, R.; Goldsmith, M.; Pleil, J.; Dary, C. J. Toxicol. Environ. Health, Part B 2012, 15 (1), 22-38.
9. Reddy, M.; Yang, R. S.; Andersen, M. E.; Harvey J. Clewell, I. Physiologically Based Pharmacokinetic Modeling: Science and Applications; John Wiley & Sons: New York, 2005.
10. Nong, A.; Tan, Y. M.; Krolski, M. E.; Wang, J.; Lunchick, C.; Conolly, R. B.; Clewell, H. J., 3rd J. Toxicol. Environ. Health, Part A 2008, 71 (20), 1363-81.
11. Gelman, A.; Bois, F.; Jiang, J. J. Am. Stat. Assoc. 1996, 91 (436), 1400-1412.
12. Eric Hack, C.; Chiu, W. A.; Jay Zhao, Q.; Clewell, H. J. Regul. Toxicol. Pharmacol. 2006, 46 (1), 63-83.
13. Toxvaerd, S. Int. J. Mol. Sei. 2009, 10 (3), 1290-9.
14. Siegel, J. S. Nature 2001, 409 (6822), 777-778.
15. Saghatelian, A.; Yokobayashi, Y.; Soltani, K.; Ghadiri, M. R. Nature 2001, 409 (6822), 797-801.
16. Ulrich, E. M.; Morrison, C. N.; Goldsmith, M. R.; Foreman, W. T. Rev. Environ. Contam. Toxicol. 2012, 217, 1-74.
17. Chang, D. T.; Goldsmith, M. R.; Tornero-Velez, R.; Rabinowitz, J.; Dary, C. C. Abstr. Pap., Am. Chem. Soc. 2007, 234.
18. Knaak, J. B.; Dary, C. C.; Zhang, X.; Gerlach, R. W.; Tornero-Velez, R.; Chang, D. T.; Goldsmith, M.-R.; Blancato, J. N. Rev. Environ. Contain. Toxicol. 2012, 219 (1), 376.
19. Kim, K.-B.; Anand, S. S.; Kim, H. J.; White, C. A.; Fisher, J. W.; Tornero-Velez, R.; Bruckner, J. V. Toxicol. Sei. 2010, 115 (2), 354-368.
20. Godin, S. J.; DeVito, M. J.; Hughes, M. F.; Ross, D. G.; Scollon, E. J.; Starr, J. M.; Setzer, R. W.; Conolly, R. B.; Tornero-Velez, R. Toxicol. Sei. 2010, 115 (2), 330-343.
21. Mirfazaelian, A.; Kim, K.-B.; Anand, S. S.; Kim, H. J.; Tornero-Velez, R.; Bruckner, J. V.; Fisher, J. W. Toxicol. Sei. 2006, 93 (2), 432-142.
22. Matsuo, T.; Mori, T. Pyrethroids: From Chrysanthemum to Modern Industrial Insecticide; Springer Verlag: Berlin, 2012.
23. Huang, H.; Fleming, C. D.; Nishi, K.; Redinbo, M. R.; Hammock, B. D. Chem. Res. Toxicol. 2005, 18 (9), 1371-7.
24. Crow, J. A.; Borazjani, A.; Potter, P. M.; Ross, M. K. Toxicol. Appl. Pharmacol. 2007, 221 (1), 1-12.
25. Ross, M. K.; Borazjani, A.; Edwards, C. C.; Potter, P. M. Biochem. Pharmacol. 2006, 71 (5), 657-69.
26. Kaneko, H. J. Agric. Food Chem. 2010, 59 (7), 2786-2791.
27. Miyamoto, J. Environ. Health Perspeet. 1976, 14, 15-28.
28. Liu, W.; Gan, J.; Schlenk, D.; Jury, W. A. Proa Natl. Acad. Sei. U.S.A. 2005, 102 (3), 701-6.
29. Soderlund, D. Arch. Toxicol. 2012, 86 (2), 165-181.
30. Soderlund, D. M.; Clark, J. M.; Sheets, L. P.; Mullin, L. S.; Piccirillo, V. J.; Sargent, D.; Stevens, J. T.; Weiner, M. L. Toxicology 2002, 171 (1), 3-59.
31. Scollon, E. J.; Starr, J. M.; Godin, S. J.; DeVito, M. J.; Hughes, M. F. Drug Metab. Dispos. 2009, 37 (1), 221-8.
32. Godin, S. J.; Scollon, E. J.; Hughes, M. F.; Potter, P. M.; DeVito, M. J.; Ross, M. K. Drug Metab. Dispos. 2006, 34 (10), 1764-71.
33. Godin, S. J.; Crow, J. A.; Scollon, E. J.; Hughes, M. F.; DeVito, M. J.; Ross, M. K. Drug Metab. Dispos. 2007, 35 (9), 1664-1671.
34. Ariens, E. J. Quant. Struct.-Act. Relat. 1992, 11 (2), 190-194.
35. Mishra, N. K. Expert Opin. Drug Metab. Toxicol. 2011, 7 (10), 1211-1231.
36. Ekins, S.; Swaan, P. W. Development of Computational Models for Enzymes, Transporters, Channels, and Receptors Relevant to ADME/Tox. In Reviews in Computational Chemistry; John Wiley & Sons, Inc.: New York, 2004; pp 333-415.
37. Zou, J.; Xie, H.-Z.; Yang, S.-Y.; Chen, J.-J.; Ren, J.-X.; Wei, Y.-Q. J. Mol. Graph. Modell. 2008, 27 (4), 430-438.
38. Wermuth, C. G.; Ganellin, C. R.; Lindberg, P.; Mitscher, L. A. Pure Appl. Chem. 1998, 70 (5), 1129-1143.
39. Sippl, W. Pharmacophore Identification and Pseudo-Receptor Modeling. In The Practice of Medicinal Chemistry, 3rd ed.; Wermuth, C. G., Ed.; Academic Press: Burlington, MA, 2008; pp 572-586.
40. Provost. F.; Kohavi. R. Mach. Learn. 1998. 30 (2). 271-274.
41. Chen, L.-J.; Ulrich, E. M.; Lindstrom, A. B., 2012, unpublished data.
42. Molecular Operating Environment (MOE), 2011.10; Chemical Computing Group, Inc.: Montreal, Canada, 2011.
43. Halgren, T. A. J. Comput. Chem. 1996, 17 (5-6), 490-519.
44. Labute, P. J. Chem. Inf. Model. 2010, 50 (5), 792-800.
45. Kolossvâry, L.; Guida, W. C. J. Am. Chem. Soc. 1996, 118 (21), 5011-5019.
46. Goto, J. AutoQuaSAR 2006.8; Ryoka Systems, Inc.: Tokyo, Japan, 2006.
47. UniProt. http://www.uniprot.org/.
48. Clark, A. M.; Labute, P. J. Chem. Inf. Model. 2007, 47 (5), 1933-1944.
49. Jakalian, A.; Jack, D. B.; Bayly, C. I. J. Comput. Chem. 2002, 23 (16), 1623-41.
50. Mobley, D. L.; Dumont, E.; Chodera, J. D.; Dill, K. A. J. Phys. Chem. B 2007, 777 (9), 2242-54.
51. Labute, P. MOE LogP(OctanolZWater) Model, 1998.
52. Wildman, S. A.; Crippen, G. M. J. Chem. Inf. Comput. Sei. 1999, 39 (5), 868-873.
53. O'Brien, R. Qual. Quant. 2007, 41 (5), 673-690.
54. Pindyck, R. S. Econometric Models and Economie Forecasts; McGraw-Hill: New York, 1981.
55. Solomonov, B. N.; Novikov, V. B.; Solomonov, A. B. Russ. J. Gen. Chem. 2002, 72 (6), 854-863.
56. Abraham, M. H.; Whiting, G. S.; Doherty, R. M.; Shuely, W. J. J. Chem. Soc, Perkin Trans. 2 1990 (8), 1451-1460.
57. Abraham, M. H. Chem. Soc. Rev. 1993, 22 (2), 73-83.
58. Buchwald, P.; Bodor, N. J. Med. Chem. 1999, 42 ( 25), 5160-5168.
59. Chaudry, U. A.; Popelier, P. L. A. J. Phys. Chem. A 2003, 107 (22), 4578-4582.
60. O'Brien, S. E.; Popelier, P. L. A. J. Chem. Inf. Comput. Sei. 2001, 41 (3), 764-775.
61. Kutter, J.; Class, T. Chromatographia 1992, 33 (3), 103-112.
62. Liu, W.; Gan, J. J. J. Agric. Food. Chem. 2004, 52 (4), 736-41.
63. Chanda, S. M.; Mortensen, S. R.; Moser, V. C.; Padilla, S. Toxicol. Sei. 1997, 38 (2), 148-157.
64. Clement, J. G.; Erhardt, N. Arch. Toxicol. 1990, 64 (5), 414-6.